This proposal describes a new methodology for the reductive coupling of ketone hydrazones and organometallic reagents for the selective formation of carbon-carbon bonds. An N-silylated N-alkyl sulfinyl hydrazone framework will be used to optimize regioselective 1,2- addition. A variety of ketones and alkylating agents will be tested systematically to determine the viable substrate scope. This chemistry may allow for the selective formation of quaternary carbons, an ongoing challenge in organic synthesis. Stereoselective formation of (E)-tri- and tetrasubstituted olefins may also be achieved This methods ultimately may be implemented for the synthesis of biologically relevant molecules.